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Charlie-Charlene Part 5

Charlene is in love, and the magic continues
After they both got their breath back, Charlene said, “Elaine, I don’t need to wake up next to you. I don’t need to wait until we both come home from work exhausted, and all we want to do is sit and veg out. I don’t need to think about this any longer. I love you. We have been best friends for a long time, and you know me better than anyone else. I know you better, too. And I do; I love, love, love you. I love the way your mouth curls when you are pissed, and I love the way the corners of your eyes crinkle up when you laugh. I love the way you can just say things, without worrying about if anyone is shocked. I love the way you cock your head to one side when you are thinking...”

“And you love the way my cock feels in you,” Elaine finished for her.

“Well, yes! Yes! And besides, who else do I know who can both take me and take me in?”

“Honey, I love you too, you know I do, but I really think you need to try dating a guy first, to make sure that doing him at the same time as he is doing you doesn’t do the same thing for you. And I know just the guy, too.”

“Oh? Who?” Charlene asked.

“Remember Tommy? That mechanical guy we both dated a couple of times?”

“He wasn’t mechanical. He was nuclear or chemical, or one of those weird engineering studies.”

“Whatever. It doesn’t matter. Well – you remember that weekend he and I went skiing? I never told you, because I was in love with you then, and was afraid you’d be hurt, but we never got onto the slopes. We never even made it out of our cabin that whole weekend. All we did was fuck like rabbits. And I probably would have stayed with him for a lot longer, but after I did him with the strap-on, I decided I just had to try it out on some girls, too. So when I got home, I ran it through the dishwasher, and then on Monday … well, you know the rest, but it’s been girls all the way ever since,” Elaine said.

“Oh yeah, I remember him. He always wanted me to peg him, and at the time, that was just such a turn-off. But after we graduated, he went to work for Brown-Bovari, someplace in New Jersey.”

“Yeah, but he quit. And you know what today is?”

“Yeah, it’s Saturday,” Charlene responded.

“No, Silly, not the day of the week, the DATE!”

“It’s …um.. August 20. OH! August 20 th ! That’s the day that new band is supposed to be playing the concert in the park this afternoon. Brass Boots. We were gonna go hear them.”

“Bingo,” Elaine said, and went on, “and guess who’s playing pedal steel for them.”

“No shit? Tommy?”

“Yep. None other. And I happen to know he’s available, because I turned his last girlfriend, and she dumped him.”

“Laine, Honey, you’re such a slut,” Charlene said with a smile.

“Well, you were dating that Bob guy and a girl’s gotta do something.”

“Don’t remind me of that son of a bitch. That night he called me Caroline, while I was blowing him, was the last straw. I damn near bit it off.“ Charlene grimaced at the memory. She had gotten out of the car at the next traffic light, and walked home.

“Okay,” Elaine said.”Sorry to bring up a sore subject. Anyway,” she glanced at the bedside clock and went on, “look. It’s just noon. We have time to get cleaned up, and go over to the park and get a couple of good seats. They don’t start playing till two, and maybe we can get a chance to talk to him before they begin. You can hook up with him, and I can just run back home. I really have to do some laundry this weekend, anyway.”


Tommy was running a few chords and licks, just to get his fingers limbered up, and scanning the crowd that was gathering, when he saw two women wander in together from the street. They looked really familiar, but he couldn’t quite place them. They walked right up to the bandstand, and it suddenly hit him. It was Charlene and Elaine, from college. He went to the edge of the makeshift stage, and squatted down to greet them.

“Hi, Tommy. How’ve you been?” Charlene asked. “I thought you were working for Brown-Bovari.”

“I did, for about a year, and then decided ‘screw it’. My dad died, and I inherited enough cash to live on for a few years, so I decided I had to give full-time playing a try. So, for the past three years, that’s all I’ve been doing. I am not getting rich, but I’m not starving, and I’m a Hell of a lot happier than I was in that cubicle. What have you been up to?”

“Oh, I’m working for a little local firm, doing hydrology and hydraulics. And guess what? I got the exam results back yesterday and I passed. So now I’m a for-real engineer.”

“Two weeks ago, you couldn’t even spell it,” Tommy said, laughing.” Hey, that’s great. Look, I gotta play this gig; all these people are out here, waiting,” he waved his arm in a broad circle. “So why don’t you stick around, and come up to the stand while I pack my shit. I’ll take you out to dinner, by way of celebration. You too, Lainie. We can rehash our old college days.”

“Ah, thanks anyway, but I already have a date tonight,” Elaine lied.

“ Okay. Some other time then. Well, I gotta go to work, before this crowd starts chanting.”


Tommy and Charlene had a good time at dinner, and Charlene was trying to figure out how to tell Tommy about her new appurtenance, when out of the blue, Tommy said, “Look, Charls, this has been great fun, and I really enjoy talking with you, but right now all I really want to do is quit talking, and jump your bones.”

Charlene stood up quickly, and Tommy had a moment of panic, thinking perhaps he’d said the wrong thing, and upset her. She looked him straight in the eye and said crisply, “Pay the fucking tab. I’ll be waiting outside.”

Tommy stood too, then, and picked up the check and looked at it. He took a fifty dollar bill and a twenty dollar bill out of his wallet, and dropped them on the table. Screw the change, he thought. The waiter will get a twenty percent tip. He quickly headed for the door, watching Charlene’s hips sway, as she walked ahead of him. He was almost to the door, when one of the diners grabbed him by the sleeve, stopping him.

“Aren’t you the guy who was playing pedal steel with that band this afternoon?” the man asked.

Tommy was a little irked that some stranger had slowed him down, just as he was about to score, so he answered brusquely,

“Yeah. So?”

“ Well, my name is …”

“Look, buddy, I don’t care what you’re selling, but I don’t want any. Now, if you’ll excuse me …”

“Arnold Karas,” the man went on, ignoring the interruption. “Here, take my card. I am a recording agent. I saw the chick. Go get her. Call me on Monday. And don’t knock her up, ‘cause you’re gonna be too busy to be having a family life.”

Tommy’s face broke into a grin as he took the card, and slid it into his jacket pocket. “Thanks,” he said, and once again headed for the door.

“Who was that?” Charlene asked him, as the door closed behind him. “You’re grinning like you just won the lottery.”

“A recording agent. He gave me his card. He wants me to call him on Monday.”

“Oh, great,” Charlene said. “Here I was, all ready to get laid, and you’re gonna be thinking about music, instead of me.”

“I have ADD,” Tommy said, as they crossed the street. “ I can think about you and completely forget music.” He looked down at her and grinned again.

“Oh all right, com’on then,” she said, laughing, and tucking her hand under his arm.


As she closed the door behind them, Tommy grabbed her, and held both her hands over her head, pinning her to the wall next to the door. He kissed her roughly, and ground his hips into hers. She could feel herself becoming aroused, and pushed back at him. Her crotch was soaked, and she could feel an erection beginning. With his other hand, he reached up and cupped her breast, feeling the nipple harden under his palm.

Then, releasing her wrists, he put his other hand down to her crotch. “WHAT THE FUCK?” he asked, loudly. “What the Hell is this?” Releasing her, he backed away, into the center of the room.

Charlene took a deep breath. “Come into the kitchen,” she said, “and grab that whiskey bottle off the shelf on your way. I’ll get a couple of glasses. Before we go any further, we need to talk.”


They were on their second glass of scotch as Charlene was finishing her story, “So I thought, if you still like to be pegged, maybe we could … well … make it work.”

Tommy’s erection had been throbbing for the past fifteen minutes, ever since Charlene had told him about how she and Elaine had managed to both give and get, simultaneously. All he could think was how good it would feel to have his ass filled and his prostate stimulated, while he was inside Charlene’s pussy. “Yes I do,” he said, “but how big did you say it is? May I see it?”

“Let’s go in the bedroom,” she replied, “and take our drinks with us.”


“Ow!” Tommy exclaimed. “It doesn’t bend that way when it’s hard.”

“Well, I have to bend it down, or I can’t reach your ass, while you’re in me,” she said in frustration.

“Well, roll over on your side, then, and I’ll jerk you off while I’m inside.”

That worked, of course, as Charlene already knew it would, and she had a satisfying, but not earth-shaking orgasm. They lay there, side by side, holding hands, and she said, “Well, if I can get this thing up again, I really ought to return the favor.”

“I’d like that, Tommy said, “but go slow. Your cock is bigger than the toys I am used to using. Will you get hard if I do this?” He reached down with his hand, and gently caressed her outer lips. His wrist rubbed against the length of her cock, and he slid a finger between her folds. She was very wet, still, and his finger slid in easily. Slowly, he began sliding his arm up and down, working his finger in and out of her opening.

Soon, Charlene had a full erection once more, and she said, “Get on your hands and knees. I want to enter you that way.” She reached to the bedside table, and grabbed the tube of KY jelly. She put a large dollop on the two middle fingers of her right hand, and began working it into Tommy’s anus.

He groaned as she pushed both fingers into him, stretching his outer sphincter. She rested a moment, not moving, as his body became accustomed to her entry. He groaned again, and she felt the inner sphincter relax, as both fingers suddenly slid deep inside. Leaving her fingers inside, and moving them gently, she reached to the bedside table with her left hand, and plucked a condom from the pile. She tore it open with her teeth, and rolled it onto her engorged cock. Thank God I had the good sense to buy lubricated ones, she thought to herself, as she slowly slid her fingers out and replaced them with the head of her cock. She reached around his hips, and took his cock in her still wet hand. Slowly, but firmly, she began pumping it. As she did, she pressed her cock against his entrance. With each stroke, as she pulled him towards her, she could feel her cock going in a little further. Suddenly, he relaxed, and she slid deep inside. Her balls slapped against his, and he moaned loudly.

“Am I hurting you?” she asked, concerned.

“No. it just feels so good, especially when you hit that spot.”

It felt good to her, too, he was so hot, and so tight, and she could feel herself getting harder. But then, just as she was thrusting, and he was moaning, she felt something that felt like tearing inside of him. She withdrew quickly, and saw that the condom had broken. By then she was so excited she just pushed back inside. He clamped down on her hard, then, as his cock began spurting, and that drove her over the top, and she came, too. She could feel her semen squirting deep inside him, and they both collapsed, exhausted.

They fell asleep then. HeE was on his stomach, and she lay atop of him, with her now softening cock still inside him. Sometime in the night, they rolled over, and she slid out. She reached down with one hand and pulled the covers over them both, and they slept on.


The sun was streaming in the window when Tommy woke up. He looked, bleary-eyed, at the bedside clock. Ten AM it said, He got up, and padded into the bathroom to relieve himself. He stood there, scratching his head with one hand while he aimed with the other, and started to urinate. “WHAT THE FUCK?” he yelled, as the yellow stream ran down his leg. “HOLY SHIT!”

His yelling woke Charlene from a sound sleep. She had just been dreaming about helping Elaine do laundry, by putting her cock in her ass. Every time Elaine dropped another piece of clothing into the machine, Charlene thrust her cock deeper into Elaine’s ass. She sat straight up in bed, fully awake, and called out, “Tommy, are you all right?”

“Yes. No. I don’t know. This is weird. I think something is broken,” came the muffled reply.

Charlene had long felt that there were certain times that men and women, no matter how well they knew each other, needed privacy, but she got out of bed, and ran to the bathroom door. Flinging it open so hard that the doorknob punctured the wall, she stood there gawking, just as the last of his stream was running down the inside of Tommy’s leg onto the floor. The back of her hand flew to her mouth. Instinctively she knew what had happened.

“Tommy,” she said, “put your hand behind your nuts, and tell me what you feel.”

He reached down, and tentatively put two fingers behind his scrotum. His breath caught, as he felt an electric shock go from his crotch straight up his core. “Oh. My. God. I have…Holy shit. What is this? There’s a … oh shit… there’s a …a…,” he stammered.

“A vagina?” she finished for him.


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